


Keeping Watch

by Weiterlesen



Series: Can’t leave well enough alone [1]
Category: Critical Role (Web Series)
Genre: Blowjobs, Cunnilingus, F/M, Fluff, Rough Sex, Silence Kink, Smut, Tail Kink, Vaginal Sex, and some angst, fun times right outside xhorassic park, i know canonically the only way widojest is happening is if fjorester collapses, i think it’s very sexy of me to ignore jester’s attraction entirely, since i don’t want to write that right now, so stop here if you’re only here for sex and good feels, the later part will have more plot, this isn’t bashing the ship but
Language: English
Status: Completed
Published: 2019-03-24
Updated: 2019-03-23
Packaged: 2019-11-29 00:15:19
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,147
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18215585
Author URL: https://archiveofourown.org/users/Weiterlesen/pseuds/Weiterlesen
Summary: A retelling of the watch that Jester and Caleb shared in e51.





	1. Silence before the Storm

**Author's Note:**

> It was a fun convo, and I enjoyed if for that simple humor between the two of them as they discussed some of their feelings, but I, at the very least, always wish for more.

The first watch that night in the endless tunnels began with quiet words and soft touches. The battle that day was exhausting yes, but Caleb knew well that certain perceptive members of the Big No were prone to keeping one ear open so to speak. 

Deep sleep for the others would come with time, and the two of them had hours of that. So they started with small conversations. Talk of the day’s battle, of how much Nugget had grown, of how Xhorhas would be.

Eventually, the soft touches slid under clothes. Caleb kissed every inch of her as he removed her leathers. Jester made a show of sniffing his coat and shirt as they came off.

Caleb could barely hold in his laugh. “Wouldn’t want to wake them up, huh?” Jester asked, shamelessly naked in the dim light of the cloth covered dancing lights. All the bars of tension in his shoulders slid away for a moment as Caleb had an idea. 

He released the lights and found Jester’s hand by memory in the dark. He laid his coat on the ground barely ten feet from Beau’s head, and did the same to Jester. “Uh, Caleb,” Jester whispered, “shouldn’t we move farther?”

“Wouldn’t want to wake them up, huh?” Caleb parroted.  
“Well that’s just rude-“ Jester began, before being silenced with a kiss that brought their hands to the other’s cheeks. Caleb pulled back for a moment and slid out a leather strap he used for his magic with one hand, and brought both of Jester’s above her head with the other.

Jester could’ve stopped him easily, but she knew Caleb would never hurt her with his wits intact. And judging from the smile that crossed his face, oh were they ever.

With a deft hand, her hands were bound, and Caleb sunk down to kiss her again. As she brought them down to pull him closer, he crooned to her ear, “Keep them above your head, blueberry, or I’ll stop,” and sunk his head between her bare thighs. 

She complied with a nod, and in a couple moments, broke her promise as her bound hands dropped to her mouth to block a whimper that nearly escaped.

“I’ve barely started, my love. Keep them up there, I know you can do it”

She nodded again, and spent the next few minutes in the most unbearable heaven she could imagine. When Caleb brought his fingers to her, she couldn’t help but let out the tiniest squeak. 

She nearly gave herself whiplash as Beau made some small noise and she jerked her head to stare at her friend. She nearly squeaked again as Caleb’s beard scratched up her leg when he did the same. 

At a small motion from Caleb, Frumpkin walled over to Beau and nuzzled onto her. Beau fell back to sleep with arms full of cat and making a soft noise that an uncharitable (and unwise) person might call a snore.

The two lovers let out small sighs of relief and Caleb gladly returned to Jester’s torture. She spent what felt like hours in the most lovely and caring hell she could imagine. Jester had to wonder if the damn Zemnian had any tiefling in his blood to gift him this devil’s tongue. _Could he have studied this?_ she pondered offhandedly.

Finally, she felt herself growing close, and her thighs began to tense up, bringing him even closer to her. The cool of the coat at her back helped to distract from his blisteringly hot fingers, but she felt her heart speeding up regardless. And, just as the moment was about to erupt, the bastard pulled back.

“What the fuck Caleb? My arms are still up here!” Jester stage whispered at him, gesturing with her hands. 

The bastard smiled, “You were going to scream, so I stopped.” He idly ran his hand up her tail and she hissed and tensed and closed her eyes, yet he stopped again.

She opened them to find his eyebrows raised. “What?” She glared at him, “Tails get sensitive like everything else when you’re licking my pussy. I could suck your cock until you were like I am and pulling your cheek would send you over.”

“I guess I just didn’t expect it was all.” He said, and sat back, doing nothing for a second but staring, entranced, at her tail.

Jesters heart rate began to settle against her wishes, and was just wondering if she’d have to rub herself on his leg to get him to do something when he ran his tongue along her tail and she was back where she was before. “Fucker, just let me come already.”

“I don’t think so, I’m having fun,” he replied.

“Fuck you.” She pulled her hands out of the strap and pushed Caleb against the cave wall behind him. 

She smiled her best, “Be quiet right?” And slid down his trousers. Her mouth began to work swiftly, and, not taking near the time he had, she had him the same way she had been. 

“Jester,” he whispered, his eyes open and pleading, “please.” His pride was gone in a heart beat. She had wanted to drag it on longer, but she could hardly blame him for loving her mouth given the way she loved his. He finished quietly, like he did most things, and, for a moment, the look in his eyes was a dream to her.

They lay together, as they always did, and she was grateful for the warmth. She started to realize the coolness of the tunnels on her naked body once the great fire they’d made together was petering out.

After a time, Caleb slid down her back, and she almost laughed as he started feeling her tail again. “It’s not gonna work now, silly.”

“I guess so, but...” One hand moved from her tail and found its way to her chest, and another landed between her legs. “You didn’t get to finish did you?”

“No, but it’s fine, some of the others will be waking soon for the next watch,” she paused, “not that we did much of that though,” and a chuckle turned into a low moan.

“Remember, darling, be quiet, especially if they’re gonna wake up soon.” Caleb mumbled out, his mouth already lost to the devastating attack it began between her legs. 

“Fuck that.” She mumbled back, and with a quick clasp of her fingers and more mumbling, the soft sounds from their sleeping party disappeared, as a bubble of silence formed around the lovers. 

Jester flashed him a grin over her shoulder as she shifted and leaned back, sending him onto his own. She found his dick between her legs and stroked it until he was ready. Tossing her head back, she sank down onto him. 

Caleb loved this cursed hell as much as he loved anything in this world, as his deity of a lover rode him, teasing him with what he could see, and what he couldn’t. 

He worshipped her with his eyes, with his hands. Her hair bouncing, the tips of her horns glinting, a flash of a smile over her shoulder before facing forward again, and her head falling backward in a groan he couldn’t bear not to hear, not to feel vibrate in her chest and on his. 

He pushed her forward as he got up, just like she’d been waiting for. She loved him like this, when he was pushed to his limit and forgot restraint for a time.

He ground himself into her hard, her body under his, one hand at her chest, one around her neck, not squeezing, but it hardly seemed to matter to her when just the feeling of him around her took her breath away. 

Her eyes fell forward, and she saw the edge of the bubble as a shimmering light only she could perceive, and her face was only inches from it as he rammed into her over and over. 

It was only moments later that he finished inside her. Damn was she gonna have to pray for that not to bear fruit; how much need and desire he was pouring into her. 

Her back arched into him as she screamed her silent scream and finished around him. Her body was mush, and it took Caleb what could’ve been five minutes or could’ve been fifty to pull himself out of her, get her into her nightgown, dress himself, and recast the tiny hut. 

He whispered into her ear, “Next time, cast it on them, and not on us, I want to hear you if I can, and he stumbled to his coat.

He was just in time as Beau opened her eyes, and placed a hand on Yasha’s shoulder to wake her, watching as Caleb fell onto his jacket next to Nott and Jester, fast asleep in moments, with a soundless, dreamless sleep that lasted until a hand cupped his face, and he woke to Jester smiling at him again. 

It was the next day, time to walk the tunnel again.


	2. A Quiet Epilogue

**Summary for the Chapter:**

> Caleb tells Jester a story to help her sleep after the demons attack and all the friendly fire.

**Notes for the Chapter:**

> I was going to include a simplified version of this as a sort of mini conversation between Jester and Caleb in the last chapter between the two events, but it felt a bit like the single watch was being filled out, and I didn’t want to drag it out too much. So here it is now, on another night (where it’s probably needed more tbh). And no sex this time, sorry y’all.

“Tell me a story, Caleb” Jester asked, whispering into his ear after the hut was cast, and the party fell to their packs. She was entirely too close for even the pretense of separation, even though most of the group already knew about or suspected them. 

Maybe nobody would notice if they didn’t speak, maybe everyone was so tired after the demons that they’d be deaf for the night.

Caleb took out a wire and whispered his message. “What kind of story?”

“A bedtime story,” said the reply

“I don’t know many of those”

“Any will do”

“They’re all Zemnian”

“Just like you”

“They’re not all that happy”

“Just like you”

He grins.

“So there are these three cats”

“That’s how you start a story?” She asked incredulously.

“A Zemnian one, ja” He replied.

She pauses for a moment, “You may continue,” she says, finally.

“The three cats are named Salt, Pepper, and Mustard. They have an owner, and one day while they’re out walking, another man comes by”

“Why would you walk cats?”

“It originally had dogs, but I prefer cats.”

“I understand, continue.”

“The new man had three sheep, and the cats’ owner sells them to him for the sheep”

“Would you sell your cat for a sheep?”

“No, and can I continue without the color commentary? This is a bedtime story, ja?”

“Ok, keep going.”

“The owner sells the cats, and they have a new owner. These cats are very good, and have special powers. 

Salt brings food no matter where they are, Pepper destroys enemies no matter how powerful, and Mustard can bite apart any metal no matter how strong. 

After getting to know their new owner, the cats and the man hear of a dragon that has kidnapped a beautiful princess, and will eat her that night.”

Caleb’s mind flashes with images for a moment. Jester. All alone in the dragon’s lair. He begins to shake, before the Jester in front of him places her hands on his. She’s terribly tired, just as he is, and she can still look at him so sweetly. She waits until he’s still, and closes her eyes. He continues.

“They ride over in a coach and, with the help of the cats’ great powers, the owner saves the princess and kills the dragon. 

The princess wishes to marry him, but the owner has his own mission, and so promises to return in three years when he has finished his goals. 

And he leaves.”

He wonders what he’ll do when Trent is dead and the mistake is fixed. He thinks Jester might be fast asleep, but he continues anyway.

“When he returns, he finds that the princess will be married in a week, and when he claims he killed the dragon, the cats and he are arrested, for the coachman who drove them there and back three years before claimed he did the deed.

Prison isn’t an issue for the cats. Mustard breaks the bars on the window, and Salt brings them all food fit for royalty.

Salt got that food from the princess, who has recognized the cat. 

She finally gathers the courage to tell her father the truth, after having been intimidated by the coachman before to lie, and the cats and their owner are freed.

The owner and the princess get married, and the cats live in luxury for the rest of their lives.”

Caleb is barely awake himself at this point, and the wire slides from his grip.

“I think you focused too much on the cats, and not enough on the brave owner, who faced a dragon and saved a girl just for the good of it, even when he had his own ambitions.” Jester replies, her grin unmistakable, even in the dark.

Caleb grins to the tunnel, and slips off to sleep.

**Notes for the Chapter:**

> This is based on a german fairy tale I read a while back called the three dogs, but I figured Caleb would call it something else, along with telling more from the cats’ point of view. Also I’m actively writing the next part of this, and it’s more plot heavy and with angst, so if anyone could recommend a beta, I’d appreciate it.

**Author's Note:**

> One more chapter and then the next part is just gonna be a lot of angst sorry.


End file.
